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Despite how deeply entrenched in the 1960s he appears, “Mad Men” creator Matthew Weiner admits the new season chronicles the first portion of the decade that he was actually alive to experience himself.

As Weiner prepares the deliver the long-awaited fifth season of his beloved, critically acclaimed AMC series and all of its top secret storylines, PopcornBiz caught up with the man who gave the world Don Draper and got a peek inside his thought process as he pushes the series forward and intertwines the characters’ personal lives with the ‘60s moments and movements that resonate with him.

Tell us about your vision for this season going in.

Going into the season, doing it for the fifth time I thought that I would have more confidence, and then it takes you over: the anxiety of refusing to do the same thing. No one will see something that they've seen before, as far as I can tell. I think that people don't change, so the characters are consistent, but I refused to do the same thing. So that immediately, on the one hand, keeps you from being bored, and on the other hand makes you feel sick to your stomach…I always feel like 'Okay, we're here this season and instead of freaking out and trying to go better than that I will just go over here and try and do something, not laterally, but just something different.’ New and good are not related to each other. All I wanted to do was say, 'You're going to come back to the show; you're a fan or not a fan – Are you going to be happy to be there? Are you going to be stimulated? Are you going to be engaged?' The showman part of me was like, 'I should – without making the show too extreme – go to the things that I'm interested in emotionally.' I think there's a very consistent story being told. I think it's got a lot of surprises in it and I think that when we came at the end of it there's this thing about reaching a point in your life and hoping that you will finally understand what's going on and that some wisdom has been achieved. The world keeps moving around you and you can never get your feet on the ground. You either end up being the person who's wearing the clothes that you had in high school and saying, 'What's going on around here?' or you can try to keep up with it and a lot of times look stupid. 'Who does he think it is?'

Do you look at each new season of “Mad Men” with a theme in mind?

No, I go into it with something, but it's not really like…what it is, is I sort of think of where Don is in his life. It all derives from Don – there's no question about that. That's the main character. I do all the characters, obviously, and I have lunch with Jon Hamm where we talk about Don and we talk about our lives. I sort of think about where I am in my life and where the world is and it's sort of my job as a writer to key in on that, hopefully – or at least what I think it is. I don't try to think for other people. Then I say 'This is probably the next chapter, this is where you go in life.' I've committed to how old they are, to where they're from. Then I get to bring in new people, but I know what that story will be and I usually get, in a very nonintellectual way, a feeling about where it's going to go. Then images come to me. I've been very lucky to have that happen.
What's your ideal gap between seasons and airdates?

I'd like to be on every year, I'll just say that right now. This was never my intention, and quite honestly I know it's impossible to clarify this story, but I'm going to do it one more time: part of my negotiation was about making sure the show was on last year. I have accepted the fact that it's not, and I'm excited that here we are. The only thing that I can say is that I'm glad that we had such a controversial finale, because I think that if the show had ended in a more languid way I don't think that people would've been as interested in what's coming. It was the most cliffhanger-y of the shows that we'd had.

Is every year of the ‘60s as fascinating as the last for you?

They're all different…The show is not a history lesson, but what I love is seeing what was considered to be a big event and how it was being processed by people at the time and how that informs how we're living right now. We have no idea what are the key events that are going on. There are moments that go in to the history books as the big turning point…but I go back to what I have said before, which is that your personal experience does not always interact with that – having lived through something like 9/11 and the thing that always blew my mind when when people said, 'Oh, you're going to do the Kennedy assassination,' I’d remind people who lived through that event that Thanksgiving was the next week. They were like, 'It was?' I said, 'What was that Thanksgiving like?' They say, 'I don't remember. All I remember is that we had Thanksgiving.' So that to me is like if you're in the middle of a divorce and there is the Cuban Missile Crisis, your problem is bigger. That's the thing that I've enjoyed about seeing history processed. Also, just to see something in the newspaper, like terrible reviews for 'West Side Story' or something – I don't want to be smug about it. That's kind of fun, or 'Doctor Zhivago.' That was something that they really through under the bus. Oh, my God, they said, 'This is an old fashioned movie and there's no story and who are these actors? It's so boring.' And then it played for like nine years. You can open anything in the entire ‘60s, anything that has listings and see 'Doctor Zhivago' playing somewhere…There are songs that play that are so dissonant when they come out that they become rejected and then…I don't think that my parents that one of their nieces or nephews would get married to 'I Get By With Little Help From My Friends,' that that would be playing when they went down the aisle. That was a pop song and it says ‘I get high in it.’ There's all these things in it, and the culture adjusts to that.

Can you talk about what Jessica Pare, who played Don’s secretary-turned-fiancé, brings to the show?

She's a great actress and we're finding things to do with her. She is part of the show this year. We said that on some level. Jessica Pare is a very gifted actress who is a great beauty and has been a joy to work with. She has great training. She's like a physical actress who understands what she's doing. To me, what I really love about her is that she believes in the show and really trusted me. I never told her where that storyline was going. This is a woman who's been the lead on shows. She trusted me with one or two lines for many, many episodes and just went with it. I just like it because it's just someone new and fresh and she has this continental quality. To me she looks like one of those actresses from the French movies that I love. Sally Draper’s emerged as an equally fascinating character as her parents. Will you still be exploring the younger characters?

I cannot tell you about her story, but Kiernan [Shipka] is a big part of the show as always, and in addition to all of the good fortune that I've had with casting, to find someone at that age who has developed and to see their natural talent come out, at this point I don't even think about it anymore. I had a meeting with her mother at the beginning of the year and I was like, 'Well, this year she's going to do blank, blank, blank,' and Erin, Keirnan's mother, said to me, she said before she came to visit me this year that Kiernan had said to her, 'Mommy, don't say no to anything. He gives me great stuff.' She never has, honestly. There is an honesty about childhood and Kiernan is aware of that and she's a very old soul. It's not a cliché…You will see the reality of a little girl's life at that period. For me it's super-important to keep her story alive because she is an entry point for a lot of the audience. I'm not her age, but I remember and see a lot of things through my childhood. Last season was the first season where I had actually even been on the planet while the show was going on. But I always attributed it to the fact that I lived in Baltimore until I was eleven and it was 1965 in Baltimore until about 1980.

Published at 1:28 PM EDT on Mar 22, 2012 | Updated at 2:48 PM EDT on May 30, 2012